Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
Winchester
Check in / Check out
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Search by region
I’m flexible
I’m flexible
Europe
Europe
Canada
Canada
Caribbean
Caribbean
Italy
Italy
South America
South America
Check in
Add dates
Check out
Add dates
Who
Add guests
Search
Airbnb your home
Sign up
Log in
Airbnb your home
Help Centre
%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Your search
Skiing
Countryside
Cabins
Amazing pools
Amazing views
Rooms
Farms
Vineyards
Lakefront
Chef's kitchens
Play
Bed & breakfasts
Ski-in/out
Tiny homes
Design
Barns
Grand pianos
Trending
New
Off-the-grid
Camping
Mansions
A-frames
Golfing
Creative spaces
OMG!
Yurts
Treehouses
Lake
Filters
, 1 filter applied
1
Display total before taxes
Show map
Search results; 219 places in Winchester
219 places in Winchester
Guest favourite
Guest favourite
Cabin in Colebrook
Adorable, storybook log cabin
6 beds
6 beds
21–26 Apr
21–26 Apr
₹24,157
night
₹24,157 per night
4.94 out of 5 average rating, 196 reviews
4.94 (196)
Guest favourite
Guest favourite
Home in New Hartford
Mountain Serenity Lake View Pool & Hot Tub
5 beds
5 beds
21–26 Apr
21–26 Apr
₹57,294
night
₹57,294 per night
4.9 out of 5 average rating, 10 reviews
4.9 (10)
Guest favourite
Guest favourite
Cottage in Litchfield
Litchfield - Hot Tub - Mohawk Mountain - Fireplace
3 beds
3 beds
4–9 May
4–9 May
₹18,581
₹13,841
night
₹13,841 per night, originally ₹18,581
4.89 out of 5 average rating, 254 reviews
4.89 (254)
Guest favourite
Guest favourite
Cottage in Southwick
Lake Views from Hot Tub Kayaks Fire Pit Central AC
4 beds
4 beds
27 Apr – 2 May
27 Apr – 2 May
₹26,610
night
₹26,610 per night
4.97 out of 5 average rating, 63 reviews
4.97 (63)
Guest favourite
Guest favourite
Home in Goshen
Charming renovated farmhouse with hot-tub
5 beds
5 beds
18–23 Apr
18–23 Apr
₹19,505
night
₹19,505 per night
4.9 out of 5 average rating, 48 reviews
4.9 (48)
Guest favourite
Guest favourite
Guest suite in Granby
Onomea Farm
3 beds
3 beds
23–28 Apr
23–28 Apr
₹17,826
night
₹17,826 per night
4.97 out of 5 average rating, 60 reviews
4.97 (60)
Superhost
Superhost
Cottage in Kent
NEW - Hot Tub - Mohawk Mtn - Appalachian Trl
3 beds
3 beds
21–26 Apr
21–26 Apr
₹16,034
₹10,617
night
₹10,617 per night, originally ₹16,034
4.88 out of 5 average rating, 149 reviews
4.88 (149)
Guest favourite
Guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 beds
3 beds
25–30 Apr
25–30 Apr
₹26,112
night
₹26,112 per night
4.99 out of 5 average rating, 201 reviews
4.99 (201)
Home in Morris
Luxury Compound, Pool, Hot Tub and much more.
7 beds
7 beds
1–6 May
1–6 May
₹81,622
night
₹81,622 per night
New place to stay
New
Guest favourite
Guest favourite
Cottage in Burlington
Cozy Cottage w/Lakefront Views, Swim Spa & Firepit
4 beds
4 beds
30 Apr – 5 May
30 Apr – 5 May
₹31,895
night
₹31,895 per night
5.0 out of 5 average rating, 40 reviews
5.0 (40)
Guest favourite
Guest favourite
Home in Cornwall
The Owl Cottage@Mohawk Mountain
3 beds
3 beds
26 Apr – 1 May
26 Apr – 1 May
₹21,819
night
₹21,819 per night
4.98 out of 5 average rating, 48 reviews
4.98 (48)
Guest favourite
Guest favourite
Guest house in Cornwall
Charming Guest Cottage with Private Pool
1 bed
1 bed
8–13 May
8–13 May
₹30,346
night
₹30,346 per night
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favourite
Guest favourite
Home in Bethlehem
Lakeview Expanse
4 beds
4 beds
4–9 May
4–9 May
₹48,710
night
₹48,710 per night
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Guest favourite
Guest favourite
Cabin in New Hartford
Serenity Woods
8 beds
8 beds
22–27 Apr
22–27 Apr
₹1,25,227
night
₹1,25,227 per night
4.95 out of 5 average rating, 20 reviews
4.95 (20)
Guest favourite
Guest favourite
Home in New Marlborough
Berkshires Colonial Farmhouse
7 beds
7 beds
19–24 Apr
19–24 Apr
₹51,034
₹28,672
night
₹28,672 per night, originally ₹51,034
4.95 out of 5 average rating, 21 reviews
4.95 (21)
Guest favourite
Guest favourite
Cabin in New Milford
Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit
2 beds
2 beds
19–24 May
19–24 May
₹21,987
night
₹21,987 per night
4.99 out of 5 average rating, 91 reviews
4.99 (91)
Home in Monterey
Forget-Me-Not by AvantStay | Bold Lakefront Escape
8 beds
8 beds
24–29 Apr
24–29 Apr
₹66,552
₹42,876
night
₹42,876 per night, originally ₹66,552
4.9 out of 5 average rating, 21 reviews
4.9 (21)
Guest favourite
Guest favourite
Home in Great Barrington
Jaw dropping mountain & lake views
4 beds
4 beds
5–10 May
5–10 May
₹57,294
night
₹57,294 per night
4.96 out of 5 average rating, 212 reviews
4.96 (212)
1
2
3
4
…
13